Willowcroft Farm Vineyards – Leesburg, VA
38906 Mount Gilead Rd, Leesburg, VA 20175
Willowcroft Farm Vineyards is the oldest winery in Loudoun County, offering guests a peaceful, scenic retreat atop the Catoctin Ridge. This family-owned vineyard combines over four decades of winemaking experience with a deep respect for Virginia’s agricultural heritage. Known for its small-batch wines, stunning views, and warm hospitality, Willowcroft is a favorite among wine lovers seeking a more authentic and intimate experience. The vineyard’s historic red barn tasting room and surrounding views provide the perfect backdrop for a relaxing day of wine tasting. From their estate-grown Chardonnay to their bold reds, every bottle reflects a legacy of excellence.
Interesting Facts:

Wine Tasting Flights
Willowcroft’s wine tasting flights are a highlight of the guest experience, designed to showcase the winery’s craftsmanship and variety. Each tasting features 5 to 6 wines, including seasonal selections and estate-grown staples like Cabernet Franc, Riesling, and Chardonnay. Guests are guided by knowledgeable staff who share background on the vineyard, winemaking techniques, and tasting notes. This educational approach helps visitors develop a deeper appreciation for local wines and allows them to discover new favorites. The tasting room, housed in a historic red barn, adds character and charm to the experience. Flights can be enjoyed indoors or on the deck, weather permitting. Each tasting is tailored to ensure all guests—from beginners to connoisseurs—feel welcome and engaged. It’s a relaxing way to spend the afternoon while taking in panoramic views of the Virginia countryside. Visitors often purchase bottles or join the wine club after their tasting.
Outdoor Picnics & BYO Food
Willowcroft encourages guests to bring their own picnics and enjoy wine on their scenic property overlooking the rolling hills of Loudoun County. The outdoor picnic areas are thoughtfully arranged across the grounds, offering both sunlit and shaded options. Whether celebrating a special occasion or just taking in the fresh air, the natural beauty of the vineyard enhances the experience. Guests can purchase bottles from the tasting room to enjoy with their meals, making for a custom and leisurely wine-and-dine afternoon. The vineyard’s peaceful location attracts those seeking a serene, slower-paced alternative to busier wineries. Blankets and lawn chairs are also welcome, and there’s ample space for small groups to spread out. Seasonal flowers and mature trees create a postcard-worthy backdrop ideal for photos. Visitors are asked to respect the grounds and follow posted guidelines to ensure everyone’s enjoyment. It’s a flexible, budget-friendly way to enjoy fine Virginia wine in nature.


Winery Tours & Behind-the-Scenes Experiences
Willowcroft Farm Vineyards offers guided tours that reveal the history, process, and passion behind their winemaking legacy. These tours take guests from the vine to the bottle, starting with a stroll through the vineyard rows where grape varietals are explained. Visitors then step inside the production area to learn about fermentation, aging, bottling, and the science that brings each vintage to life. Staff are passionate and informative, answering questions and sharing stories that bring personality to the process. The historic red barn—once a dairy facility—now houses winemaking equipment and adds rustic charm to the tour. Seasonal tours also highlight the harvest process, giving guests an insider’s view of crush season. It’s ideal for wine lovers who enjoy learning the “how” behind what they sip. Tours end with a tasting that ties together the journey of the grapes. Guests leave with a deeper appreciation for Virginia wine and a memorable connection to the vineyard.
Willowcroft Farm Vineyards, Virginia Taxi
We provide tasting room drop-offs, roundtrip winery tour rides, picnic day transportation, group event shuttles, and charter service for special occasions at Willowcroft Farm Vineyards. Our drivers are familiar with the backroads and rural routes that lead to this hilltop winery and ensure prompt, safe, and friendly service.